DEAD

(Diethyl Azodicarboxylate)

Other Names:

1,2-Ethoxycarbonyl diazene

Diethoxycarbonyldiazene

Diethyl azodiformate

General Information:

Structure:

CAS Number: 1972-28-7

Molecular Weight: 174.15 g/mol

Appearance: Red/orange liquid

Diethyl azodicarboxylate (DEAD) is commonly used in Mitsunobu reactions. It is often used as a 40% solution in toluene. Similar reagents include DIAD, DtBAD, and ADDP.

Common Uses:

Reagent in Mitsunobu reactions

Procedure excerpt:

To a solution of A (400 mg, 1.54 mmol), B (621 mg, 3.09 mmol), and PPh3 (610 mg, 2.32 mmol) in THF (5.5 mL) at RT was added DEAD (404 mg, 2.32 mmol) in THF (0.5 mL). . . .

[full procedure]

Safety:

Diethyl azodicarboxylate (DEAD) is toxic. DEAD can explode violently at high temperatures.

References:

1) Patent Reference: WO2007117607, page 312, (12.9 MB)

2) Wikipedia: Diethyl azodicarboxylate (link)

3) www.sigmaaldrich.com: Diethyl azodicarboxylate solution (link)

4) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis; Activating Agents and Protecting Groups